12-02272. Chonemorphine [Archived]
Nomenclature
CAS number: 4282-07-9
(3β,5α,20S)-N20,N20-Dimethylpregnane-3,20-diamine; 3β-amino-20α-dimethylamino-5α-pregnane. C23H42N2; mol wt 346.59.
C 79.70%, H 12.21%, N 8.08%.
Description and references
Antiamebic principle from bark and leaves of Chonemorpha macrophylla G. Don, Ch. fragrans Alston, and Ch. penangensis Ridl., Apocynaceae: Greshoff, Ber. 23, 3545 (1890); Das, Pillay, J. Sci. Ind. Res. 13B, 602, 701 (1954); Chatterjee, Das, Chem. Ind. (London) 1959, 1445. Structure and synthesis: eidem, ibid. 1960, 290; Janot et al., Bull. Soc. Chim. Fr. 1962, 111. Stereochemistry: Chien et al., J. Org. Chem. 29, 315 (1964).
Properties
Bitter crystals, mp 149°. [α]D +25° (chloroform). Sol in chloroform, ether.Derivative
N-Benzilidenechonemorphine.C30H46N2; mol wt 434.70.
C 82.89%, H 10.67%, N 6.44%.
Properties
Crystals, mp 182-183°. [α]D +36°. uv max: 248, 277, 287 nm.Derivative
N-Acetylchonemorphine.C25H44N2O; mol wt 388.63.
C 77.26%, H 11.41%, N 7.21%, O 4.12%.
Properties
Crystals, mp 262-265°. [α]D +17°.Status
This monograph has been retired and is no longer subject to revision or update.